Catechol → 1,4-Benzodioxan 2-ethylcarboxylate

HRID 428375Notes

Reaction equation

HRID 428375 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[OH:8].C(=O)([O-])[O-].[K+].[K+].[C:15]([O:19]CC(Br)Br)(=[O:18])[CH2:16][CH3:17]>CC(C)=O>[O:1]1[C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=2[O:8][CH2:16][CH2:15]1.[CH3:17][CH2:16][C:15]([O-:19])=[O:18]

Participants

5

Reactant 3

HCID 289CatecholHCID 11430Potassium CarbonateHCID 18358931Dibromoethyl propionate

Product 1

HCID 867575721,4-Benzodioxan 2-ethylcarboxylateYield 699.4%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Ortho-dihydroxybenzene (11 g, 100 mmol) and anhydrous acetone (70 mL) were refluxed under nitrogen. Potassium carbonate (5 g, 36 mmol), dibromoethyl propionate (6.56 g, 25.3 mmol) were added portion-wise in sequence over a period of 1.5 hours. After 4 hours, the reaction was completed, which was confirmed by thin film chromatography. The crude product was cooled to room temperature, concentrated under reduced pressure to remove acetone, added with NaHCO3 solution, and extracted with ethyl acetate. The organic layer was dried with anhydrous sodium sulfate, and condensed to afford 18.51 g the product (89% yield).

Workup

  1. concentrationconcentrated under reduced pressure
  2. customto remove acetone
  3. additionadded with NaHCO3 solution
  4. extractionextracted with ethyl acetate
  5. dry with materialThe organic layer was dried with anhydrous sodium sulfate, and condensed

Sources & evidence

ORD record
ord-4fb2f5d7f26f44adbb411d1b768b8eeb
Source dataset
uspto-grants-2001_11
Patent number
US06313294B1

Reaction notes

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